The Unusual Mesophases and Properties Exhibited by a Family of Glycosteroids

Stephen James Cowling; Yves Queneau; John William Goodby; Fahima Ali-Rachedi; Nuno M Xavier; Stephane Chambert; Xiangbing Zeng; Laurence C Abbott; John N Moore; Feng Liu; Xiaoyang Yue

doi:10.1002/chem.202403678

The Unusual Mesophases and Properties Exhibited by a Family of Glycosteroids

Chemistry. 2025 Jan 17:e202403678. doi: 10.1002/chem.202403678. Online ahead of print.

Affiliations

¹ University of York Department of Chemistry, Dept. of Chemistry, Heslington Road, Not Available, YO10 5DD, York, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
² Universite Claude Bernard Lyon 1, ICBMS, Bâtiment Lederer, 1 Rue Victor Grignard, F-69622, Villeurbanne, FRANCE.
³ University of York Department of Chemistry, Chemistry, University Way, Heslington, YO10 5DD, York, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
⁴ Universidade de Lisboa Faculdade de Ciências: Universidade de Lisboa Faculdade de Ciencias, Centro de Química Estrutural, Campo Grande, 1749-016, Lisbao, PORTUGAL.
⁵ The University of Sheffield, Department of Materials Science and Engineering, Mappin Street, S1 3JD, Sheffield, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
⁶ Xi'an Jiaotong University, Shaanxi International Research Center for Soft Matter, State Key Laboratory for Mechanical Behaviour of Materials, 710049, Xi'an, CHINA.

PMID: 39821943
DOI: 10.1002/chem.202403678

Abstract

In this article we describe research on the synthesis and characterization of a family of "Janus" amphiphiles composed of disaccharide head groups and alkaloid units joined together via a methylene linker, and bearing a lateral aliphatic chain of varying length. The condensed phases formed by self-organization of the products as a function of temperature were characterized by differential scanning calorimetry, thermal polarized light microscopy, and small angle X-ray scattering, allied with computational modelling and simulations. Structural studies on heating specimens from the solid showed that some homologues exhibited lamellar, columnar and bicontinuous mesophases, whereas the same homologues revealed different phase sequences on cooling from the amorphous liquid. We explore these unusual results, which are revealed via supercooling.

Keywords: Liquid crystal; columnar; disaccharide; glycosteroid; lamellar.